메뉴 건너뛰기




Volumn 69, Issue 4, 2004, Pages 1290-1297

Investigation into the Allylation Reactions of Aldehydes Promoted by the CeCl3·7H2O-NaI System As A Lewis Acid

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CATALYSIS; CATALYSTS; CERIUM COMPOUNDS; CHEMICAL BONDS; IODINE COMPOUNDS; ORGANIC ACIDS;

EID: 1242307334     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035542o     Document Type: Article
Times cited : (56)

References (138)
  • 3
  • 23
    • 0012144006 scopus 로고    scopus 로고
    • XXV Summer School "A. Corbella". Gargnano (BS); Italian Chemical Society: Rome
    • (b) Bartoli, G.; Marcantoni, E.; Sambri, L. Seminars in Organic Synthesis; XXV Summer School "A. Corbella". Gargnano (BS); Italian Chemical Society: Rome, 2000; pp 117-138.
    • (2000) Seminars in Organic Synthesis , pp. 117-138
    • Bartoli, G.1    Marcantoni, E.2    Sambri, L.3
  • 27
    • 0000421996 scopus 로고
    • Trost, B. M., Fleming, I., Screiber, S. L., Eds.; Pergamon Press: Oxford
    • (f) Imamoto, T. In Comprehensive Organic Synthesis, Trost, B. M., Fleming, I., Screiber, S. L., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, pp 231-250.
    • (1991) Comprehensive Organic Synthesis , vol.1 , pp. 231-250
    • Imamoto, T.1
  • 50
    • 0037128362 scopus 로고    scopus 로고
    • The trivalent cerium ion is, undoubtedly, a hard cation in Pearson's classification: (a) Pletnev, I. V.; Zernov, V. V. Anal. Chim. Acta 2002, 455, 131-142.
    • (2002) Anal. Chim. Acta , vol.455 , pp. 131-142
    • Pletnev, I.V.1    Zernov, V.V.2
  • 53
    • 0342996701 scopus 로고
    • (c) Pearson, R. G. Science 1966, 151, 172-177.
    • (1966) Science , vol.151 , pp. 172-177
    • Pearson, R.G.1
  • 57
    • 4243893500 scopus 로고
    • and references therein
    • Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293 and references therein.
    • (1993) Chem. Rev. , vol.93 , pp. 2207-2293
    • Yamamoto, Y.1    Asao, N.2
  • 58
    • 0002446724 scopus 로고
    • Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: Oxford
    • Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 1-53.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 1-53
    • Roush, W.R.1
  • 69
    • 0037453638 scopus 로고    scopus 로고
    • More recently, another access to allylic anions is their electrochemical generation, and homoallylic alcohols were synthesized from carbonyl compounds and allylic acetates, using an electrochemical process catalyzed by iron complexes; see: Durandetti, M.; Meignein, C.; Périchon, J. J. Org. Chem. 2003, 68, 3121-3124.
    • (2003) J. Org. Chem. , vol.68 , pp. 3121-3124
    • Durandetti, M.1    Meignein, C.2    Périchon, J.3
  • 82
    • 1242268768 scopus 로고    scopus 로고
    • note
    • 2O-NaI system dispersed on chromatography silica gel was prepared by simple mixing of both reagents in acetonitrile followed by complete removal of the solvent.
  • 89
    • 1242336310 scopus 로고    scopus 로고
    • note
    • 2O.
  • 90
    • 1242268760 scopus 로고    scopus 로고
    • note
    • Unfortunately, the desired allylation did not proceed well from α,β-unsaturated carbonyl compounds (Table, entry 13).
  • 91
    • 1242291349 scopus 로고    scopus 로고
    • note
    • See the Supporting Information (SI) for details.
  • 102
    • 0003601534 scopus 로고    scopus 로고
    • Merck & Co., Inc.: Whitehouse. Station, NJ
    • The Merck Index, 12th ed.; Merck & Co., Inc.: Whitehouse. Station, NJ, 1996; p 332.
    • (1996) The Merck Index, 12th Ed. , pp. 332
  • 107
    • 0010955521 scopus 로고    scopus 로고
    • (a) The paramagnetism of Ce(III) precluded obtaining useful 1H NMR information: Hubert-Pfalzgraf, L. G.; Machado, L. Polyhedron 1996, 15, 545-549. Stecher, H. A., Seu, A.; Rheingold, A. L. Inorg. Chem. 1989, 28, 3280-3282.
    • (1996) Polyhedron , vol.15 , pp. 545-549
    • Hubert-Pfalzgraf, L.G.1    Machado, L.2
  • 108
    • 0000442394 scopus 로고
    • See also ref 8b
    • (a) The paramagnetism of Ce(III) precluded obtaining useful 1H NMR information: Hubert-Pfalzgraf, L. G.; Machado, L. Polyhedron 1996, 15, 545-549. Stecher, H. A., Seu, A.; Rheingold, A. L. Inorg. Chem. 1989, 28, 3280-3282. See also ref 8b
    • (1989) Inorg Chem. , vol.28 , pp. 3280-3282
    • Stecher, H.A.1    Seu, A.2    Rheingold, A.L.3
  • 109
    • 1242313799 scopus 로고    scopus 로고
    • note
    • 3 afforded more complicated results.
  • 121
  • 127
  • 130
    • 1242291355 scopus 로고    scopus 로고
    • note
    • For general experimental details, see the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.